106019-45-8Relevant articles and documents
Synthesis of α-carboxyphosphinopeptides derived from norleucine
Picha, Jan,Budesinsky, Milos,Fiedler, Pavel,Sanda, Miloslav,Jiracek, Jiri
experimental part, p. 1265 - 1280 (2011/09/12)
In the present study, we describe in detail the synthesis of a relatively rare class of phosphorus compounds, α-carboxyphosphinopeptides. We prepared several norleucine-derived α-carboxyphosphinic pseudopeptides of the general formula Nle-Ψ[PO(OH)]-Gly. These compounds could have important applications as transition state-mimicking inhibitors for methionine or leucine aminopeptidases or other enzymes. For the preparation of the key α-carboxyphosphinate protected precursors, we investigated, compared and improved two different synthetic methods described in literature: the Arbuzov reaction of a silylated N-protected phosphinic acid with a bromoacetate ester and the nucleophilic addition of a mixed O-methyl S-phenyl N-protected phosphonic acid or a methyl N-protected phosphonochloridate with tert-butyl lithioacetate. We also prepared two N-Fmoc protected synthons, Fmoc-Nle-Ψ[PO(OH)]-Gly-COOH and Fmoc-Nle-Ψ[PO(OAd)]-Gly-COOH, and demonstrated that these precursors are suitable building blocks for the solid-phase synthesis of α-carboxyphosphinopeptides.
Synthesis of norleucine-derived phosphonopeptides
Pícha, Jan,Budě?ínsky, Milo?,?anda, Miloslav,Jirá?ek, Ji?í
, p. 4366 - 4368 (2008/12/21)
The synthesis of norleucine-derived phosphonopeptides was achieved by BOP-catalyzed coupling of the monobenzyl ester of a N-CBz-protected phosphonate derivative of norleucine with hydroxyl moieties of derivatized lactic or glycolic acids. The complete deprotection of the product esters/carbamates was achieved in good yields by one-step Pd-catalyzed hydrogenolysis.
